WO2000015634A3 - Hiv protease inhibitors - Google Patents

Hiv protease inhibitors Download PDF

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Publication number
WO2000015634A3
WO2000015634A3 PCT/US1999/018986 US9918986W WO0015634A3 WO 2000015634 A3 WO2000015634 A3 WO 2000015634A3 US 9918986 W US9918986 W US 9918986W WO 0015634 A3 WO0015634 A3 WO 0015634A3
Authority
WO
WIPO (PCT)
Prior art keywords
dihydropyrones
protease inhibitors
hiv protease
present
useful
Prior art date
Application number
PCT/US1999/018986
Other languages
French (fr)
Other versions
WO2000015634A2 (en
Inventor
Frederick Earl Boyer Jr
John Michael Domagala
Edmund Lee Ellsworth
Christopher Andrew Gajda
Susan Elizabeth Hagen
Michael James Lovdahl
Elizabeth Ann Lunney
Larry James Markoski
Vara Prasad Venkata Na Josyula
Bradley Dean Tait
Original Assignee
Warner Lambert Co
Frederick Earl Boyer Jr
John Michael Domagala
Edmund Lee Ellsworth
Christopher Andrew Gajda
Susan Elizabeth Hagen
Michael James Lovdahl
Elizabeth Ann Lunney
Larry James Markoski
Vara Prasad Venkata Na Josyula
Bradley Dean Tait
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BR9913598-1A priority Critical patent/BR9913598A/en
Priority to CA002339275A priority patent/CA2339275A1/en
Priority to AU57802/99A priority patent/AU773567B2/en
Priority to JP2000570172A priority patent/JP2002524560A/en
Priority to US09/674,652 priority patent/US6528510B1/en
Priority to NZ510013A priority patent/NZ510013A/en
Application filed by Warner Lambert Co, Frederick Earl Boyer Jr, John Michael Domagala, Edmund Lee Ellsworth, Christopher Andrew Gajda, Susan Elizabeth Hagen, Michael James Lovdahl, Elizabeth Ann Lunney, Larry James Markoski, Vara Prasad Venkata Na Josyula, Bradley Dean Tait filed Critical Warner Lambert Co
Priority to KR1020017003109A priority patent/KR20010085780A/en
Priority to EP99969092A priority patent/EP1112269A2/en
Publication of WO2000015634A2 publication Critical patent/WO2000015634A2/en
Publication of WO2000015634A3 publication Critical patent/WO2000015634A3/en
Priority to US10/299,510 priority patent/US6852711B2/en
Priority to AU2004205322A priority patent/AU2004205322A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.
PCT/US1999/018986 1998-09-11 1999-08-18 Hiv protease inhibitors WO2000015634A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
CA002339275A CA2339275A1 (en) 1998-09-11 1999-08-18 5,6-dihydro-4-hydroxy-2-pyranones as hiv aspartyl protease inhibitors
AU57802/99A AU773567B2 (en) 1998-09-11 1999-08-18 HIV protease inhibitors
JP2000570172A JP2002524560A (en) 1998-09-11 1999-08-18 HIV protease inhibitor
US09/674,652 US6528510B1 (en) 1998-09-11 1999-08-18 HIV protease inhibitors
NZ510013A NZ510013A (en) 1998-09-11 1999-08-18 Dihydropyrones with selected heterocycles replacing the phenyls bearing polar substituents used as HIV protease inhibitors
BR9913598-1A BR9913598A (en) 1998-09-11 1999-08-18 HIV protease inhibitors
KR1020017003109A KR20010085780A (en) 1998-09-11 1999-08-18 HIV Protease Inhibitors
EP99969092A EP1112269A2 (en) 1998-09-11 1999-08-18 Hiv protease inhibitors
US10/299,510 US6852711B2 (en) 1998-09-11 2002-11-19 HIV protease inhibitors
AU2004205322A AU2004205322A1 (en) 1998-09-11 2004-08-27 HIV protease inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9994698P 1998-09-11 1998-09-11
US60/099,946 1998-09-11

Related Child Applications (3)

Application Number Title Priority Date Filing Date
US09/674,652 Division US6528510B1 (en) 1998-09-11 1999-08-18 HIV protease inhibitors
US09/674,652 A-371-Of-International US6528510B1 (en) 1998-09-11 1999-08-18 HIV protease inhibitors
US10/299,510 Division US6852711B2 (en) 1998-09-11 2002-11-19 HIV protease inhibitors

Publications (2)

Publication Number Publication Date
WO2000015634A2 WO2000015634A2 (en) 2000-03-23
WO2000015634A3 true WO2000015634A3 (en) 2000-11-16

Family

ID=22277357

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/018986 WO2000015634A2 (en) 1998-09-11 1999-08-18 Hiv protease inhibitors

Country Status (13)

Country Link
US (3) US6528510B1 (en)
EP (1) EP1112269A2 (en)
JP (1) JP2002524560A (en)
KR (1) KR20010085780A (en)
AR (1) AR043271A1 (en)
AU (2) AU773567B2 (en)
BR (1) BR9913598A (en)
CA (1) CA2339275A1 (en)
NZ (1) NZ510013A (en)
PE (1) PE20001052A1 (en)
UY (1) UY25708A1 (en)
WO (1) WO2000015634A2 (en)
ZA (1) ZA200100806B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010085780A (en) * 1998-09-11 2001-09-07 로즈 암스트롱, 크리스틴 에이. 트러트웨인 HIV Protease Inhibitors
WO2003091230A1 (en) * 2002-04-26 2003-11-06 Orchid Chemicals & Pharmaceuticals Limited Process for the preparation of 4-methyl-thiazole-5-carbaldehyde intermediate
DOP2003000641A (en) * 2002-05-10 2003-11-15 Pfizer INHIBITORS OF RNA-DEPENDENT RNA POLYMERASE OF HEPATITIS C VIRUSES AND COMPOSITIONS AND TREATMENT USED
US7148226B2 (en) * 2003-02-21 2006-12-12 Agouron Pharmaceuticals, Inc. Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
AU2005273619B2 (en) * 2004-08-18 2009-05-28 Pfizer Inc. Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
PA8792501A1 (en) * 2007-08-09 2009-04-23 Sanofi Aventis NEW DERIVATIVES OF 6-TRIAZOLOPIRIDACINA-SULFANIL BENZOTIAZOL AND BENCIMIDAZOL, ITS PREPARATION PROCEDURE, ITS APPLICATION AS MEDICATIONS, PHARMACEUTICAL COMPOSITIONS AND NEW MAIN USE AS MET INHIBITORS.
WO2009061856A1 (en) * 2007-11-09 2009-05-14 The Salk Instituite For Biological Studies Non-nucleoside reverse transcriptase inhibitors
MX2010006796A (en) 2007-12-20 2010-10-26 Pharma Mar Sa Antitumoral compounds.
FR2933982A1 (en) * 2008-07-18 2010-01-22 Sanofi Aventis NOVEL IMIDAZO-1,2-A! PYRIMIDINE DERIVATIVES, PROCESS FOR THEIR PREPARATION, THEIR USE AS MEDICAMENTS, PHARMACEUTICAL COMPOSITIONS AND NOVEL USE IN PARTICULAR AS MET INHIBITORS

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3786063A (en) * 1971-05-24 1974-01-15 Universal Oil Prod Co Thiazolethiosulfonates
WO1995014012A1 (en) * 1993-11-19 1995-05-26 Parke, Davis & Company 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents
WO1995014011A2 (en) * 1993-11-19 1995-05-26 Parke, Davis & Company 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents
WO1998019997A2 (en) * 1996-11-01 1998-05-14 Warner-Lambert Company Dihydropyrones with improved antiviral activity

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5840751A (en) * 1993-11-19 1998-11-24 Warner-Lambert Company 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents
KR20010085780A (en) * 1998-09-11 2001-09-07 로즈 암스트롱, 크리스틴 에이. 트러트웨인 HIV Protease Inhibitors

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3786063A (en) * 1971-05-24 1974-01-15 Universal Oil Prod Co Thiazolethiosulfonates
WO1995014012A1 (en) * 1993-11-19 1995-05-26 Parke, Davis & Company 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents
WO1995014011A2 (en) * 1993-11-19 1995-05-26 Parke, Davis & Company 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents
WO1998019997A2 (en) * 1996-11-01 1998-05-14 Warner-Lambert Company Dihydropyrones with improved antiviral activity

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 84, no. 21, 24 May 1976, Columbus, Ohio, US; abstract no. 150164, GUETTE ET AL.: "Preparation of amino hydroxyesters by reaction of ..." XP002126823 *
ELLSWORTH E L ET AL: "4-hydroxy-5,6-dihydro-2H-pyran-2-ones. 3. bicyclic and heteroaromatic ring systems as 3-position scaffolds to bind to S1' and S2' of the HIV-1 protease enzyme", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,GB,OXFORD, vol. 9, no. 14, 19 July 1999 (1999-07-19), pages 2019 - 2024, XP004171629, ISSN: 0960-894X *
HAGEN ET AL.: "Synthesis of 5,6-dihydro-4-hydroxy-2-pyrones ...w", J.MED.CHEM., vol. 40, no. 23, 1997, pages 3707 - 3711, XP002136420 *
VARA PRASAD J V N ET AL: "Nonpeptidic HIV protease inhibitors: 6-alkyl-5,6-dihydropyran-2-ones possessing achiral 3-(4-amino/carboxamide-2-t-butyl, 5-methylphenyl thio) moiety: antiviral activities and pharmacokinetic properties", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,GB,OXFORD, vol. 9, no. 11, 7 June 1999 (1999-06-07), pages 1481 - 1486, XP004169615, ISSN: 0960-894X *

Also Published As

Publication number Publication date
AR043271A1 (en) 2005-07-27
UY25708A1 (en) 1999-11-17
KR20010085780A (en) 2001-09-07
AU5780299A (en) 2000-04-03
US6852711B2 (en) 2005-02-08
CA2339275A1 (en) 2000-03-23
US20050075390A1 (en) 2005-04-07
AU773567B2 (en) 2004-05-27
NZ510013A (en) 2003-11-28
US20040106606A1 (en) 2004-06-03
ZA200100806B (en) 2002-01-29
JP2002524560A (en) 2002-08-06
AU2004205322A1 (en) 2004-09-23
WO2000015634A2 (en) 2000-03-23
PE20001052A1 (en) 2000-10-18
EP1112269A2 (en) 2001-07-04
US6528510B1 (en) 2003-03-04
BR9913598A (en) 2001-05-29

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